Trimethylsilyl iodide → 5-Benzofuranol, 2-phenyl-

HRID 965225Notes

Reaction equation

HRID 965225 reaction equation
[C:1]1([C:7]2[O:11][C:10]3[CH:12]=[CH:13][C:14]([O:16]C)=[CH:15][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](I)(C)C>C(Cl)(Cl)Cl.CO.[Cl-].[Na+].O>[C:1]1([C:7]2[O:11][C:10]3[CH:12]=[CH:13][C:14]([OH:16])=[CH:15][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 2

HCID 85247Trimethylsilyl iodide2×HCID 901838HCID 901838, compound

Product 1

HCID 122735235-Benzofuranol, 2-phenyl-Yield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 2-phenyl-5-methoxybenzo[b]furan (K K Thomas and M M Bokadia, J Indian Chem. Soc. 1966, 43, 713) (0.5 g, 2.23 mmol) in absolute chloroform (4 ml) was treated with trimethylsilyl iodide (0.44 ml, 3.09 mmol) and warmed at 50° C. for 48 h. A further quantity (0.22 ml) of trimethylsilyl iodide was added during this period. The reaction mixture was diluted with methanol (20 ml), treated with brine (40 ml) and extracted into diethyl ether (2×40 ml). The combined extracts were washed with aqueous sodium metabisulphite, followed by brine (40 ml) and dried over sodium sulphate. After concentration in vacuo the residue was distilled to give the title compound as a colourless solid (0.41 g, 88%) b.p. 250° C., 0.1 mm Hg (Kugelrohr).

Workup

  1. extractionextracted into diethyl ether (2×40 ml)
  2. washThe combined extracts were washed with aqueous sodium metabisulphite
  3. dry with materialdried over sodium sulphate
  4. concentrationAfter concentration in vacuo the residue
  5. distillationwas distilled

Sources & evidence

ORD record
ord-db364d1bda0d4b668941ef72e252377c
Source dataset
uspto-grants-1998_06
Patent number
US05773463

Reaction notes

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